Carbon tetrabromide → Benzyl 2-(2-bromoethyl)piperidine-1-carboxylate

HRID 1044865Notes

Reaction equation

HRID 1044865 reaction equation
O[CH2:2][CH2:3][CH:4]1[CH2:9][CH2:8][CH2:7][CH2:6][N:5]1[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11].C(Br)(Br)(Br)[Br:21].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[Br:21][CH2:2][CH2:3][CH:4]1[CH2:9][CH2:8][CH2:7][CH2:6][N:5]1[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 45358666Benzyl 2-(2-hydroxyethyl)piperidine-1-carboxylate

Product 1

HCID 58306210Benzyl 2-(2-bromoethyl)piperidine-1-carboxylateYield 74.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of phenylmethyl 2-(2-hydroxyethyl)-1-piperidinecarboxylate (1.76 g, 6.70 mmol) in anhydrous dichloromethane (29 mL) was added carbon tetrabromide (4.44 g, 13.39 mmol). The resulting solution was cooled in ice/water. A solution of triphenylphosphine (1.76 g, 6.70 mmol) in 10 ml dry DCM was added dropwise over 30 mins. After complete addition the reaction was allowed to warm slowly to ambient temperature and stirring continued overnight. The reaction solution was reduced in volume to <10 ml (opaque) and this was loaded onto a 100 g silica cartridge and purified by chromatography on a Flashmaster 2 using a gradient of 0-25% ethyl acetate in cyclohexane over 40 minutes. Product fractions were combined and evaporated in vacuo to give the title compound as a colourless oil (1.62 g).

Workup

  1. additionAfter complete addition the reaction
  2. custompurified by chromatography on a Flashmaster 2 using a gradient of 0-25% ethyl acetate in cyclohexane over 40 minutes
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-3dfef07b9c1d42f687a11f6803d7a206
Source dataset
uspto-grants-2013_10
Patent number
US08563717B2

Reaction notes

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